CN112601461B

CN112601461B - Polymethoxylated flavones as sweetness enhancers

Info

Publication number: CN112601461B
Application number: CN201980050435.8A
Authority: CN
Inventors: 向文娟; 印丹婷
Original assignee: Firmenich SA; Firmenich Aromatics China Co Ltd
Current assignee: Firmenich SA; Firmenich Aromatics China Co Ltd
Priority date: 2018-08-01
Filing date: 2019-07-30
Publication date: 2021-10-22
Anticipated expiration: 2039-07-30
Also published as: EP3758509A1; WO2020025639A1; CN112601461A; BR112020020114A2; US20210161188A1; JP2021531731A

Abstract

The present disclosure provides compositions comprising tetra-O-methyl scutellarein, hexamethoxyquercetn, or mixtures or combinations thereof, and their use as sweeteners or sweetness enhancers.

Description

Polymethoxylated flavones as sweetness enhancers

Cross Reference to Related Applications

This application claims priority to PCT application No. PCT/CN2018/097912, filed on 1/8/2018, which is incorporated herein by reference in its entirety.

Technical Field

In its various forms, the present disclosure provides compositions comprising 5,6,7,4' -tetramethoxyflavone ("tetra-O-methyl scutellarein" or "TMS"), 3,5,6,7,3',4' -hexamethoxyflavone ("hexamethoxyquercetn" or "HMQ"), or mixtures thereof, and their use as sweeteners or sweetness enhancers.

Background

The use of non-caloric (non-caloric) high-intensity sweeteners is increasing due to health concerns over childhood obesity, type II diabetes, and related diseases. Thus, there is a need for sweeteners having a higher sweetness than conventional sweeteners, such as granulated sugar (sucrose) or High Fructose Corn Syrup (HFCS). However, many non-caloric or low-caloric sweeteners may have unpleasant off-tastes and/or have an unexpected less-than-desired sweetness profile (profile).

Furthermore, it would be of interest to enhance the desired flavor perception, e.g., sweetness, of non-caloric or low-caloric or standard (caloric) sweeteners. Compounds that enhance certain flavor sensations are of great interest, not only to improve and/or enhance perceived flavor, but also to achieve certain flavor intensities with reduced concentrations of flavor components. As one example, by using an enhancer, less sweetener may be required to achieve a desired sweetness level, which may result in less calories (calories) and/or associated undesirable flavor notes/off-flavors.

Therefore, a sweetness enhancer is needed. Non-caloric high intensity sweeteners are known to have significantly higher sweetness levels than conventional sweeteners. These non-caloric sweeteners are typically added to edible (caloric) products to replace at least a portion of conventional caloric sweeteners, which results in edible products having a sweet flavor and having reduced caloric sweeteners.

In some cases, the caloric sweeteners and/or non-caloric sweeteners are combined with other components, such as surfactants, emulsifiers, gums, or other sweeteners to form sweetener compositions. These other components generally improve the physical or chemical properties of the caloric or non-caloric sweeteners. The sweetener composition may then be incorporated into the corresponding comestible product. In most cases, the sweetener or the sweetness associated therewith is rapidly released from the edible product once the edible product is consumed. This release is responsible for the sweetness perceived by the consumer.

For certain edible products, such as chewing gum and other confections, it is desirable to extend the release rate of the sweetener from the edible product once consumption of the edible product has begun. As a result, consumers enjoy a feeling of sweetness over a long period of time. However, conventional sweeteners are known to have faster release rates from the respective edible products. In this way, most of the sweetener is released quickly from the edible product immediately after consumption, and then little to no sweetener is released during the remaining life of the edible product. As an example, chewing gum containing conventional sweetener compositions is generally considered to be very sweet when the gum is initially chewed, but after a few minutes of chewing, the sweetness of the gum is considered to be significantly reduced.

Accordingly, there is a need for sweetener compositions that use sweeteners, such as non-caloric high intensity sweeteners, and provide extended release rates of these sweeteners from edible products into the mouth of the consumer. In this way, the sweetness associated with the sweetener composition may be recognized by the consumer over a longer period of time, and as a result, a prolonged perception of sweetness is perceived by the consumer.

Disclosure of Invention

In a first form, the present disclosure provides a composition comprising tetra-O-methyl scutellarein, hexamethoxyquercetn, or a mixture thereof. In some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 0.001 to 20ppm, the sweetness of the 4% w/v sucrose base is enhanced. In some embodiments, the composition is added to the 4% w/v sucrose base at a concentration of about 2 ppm.

In some other embodiments, the composition comprises tetra-O-methyl scutellarein and hexamethoxyquercetn, wherein the ratio (w/w) of tetra-O-methyl scutellarein to hexamethoxyquercetn is from 1:10 to 25: 1. In some other embodiments, the ratio (w/w) of tetra-O-methyl scutellarein to hexamethoxyquercetin is from 1:1 to 25: 1. In some other embodiments, the ratio (w/w) of tetra-O-methylscutellarein to hexamethoxyquercetin is from 5:1 to 25: 1. In some other embodiments of any of the preceding embodiments, the composition further comprises at least one additional sweetener, such as an artificial or natural sweetener.

In a second form, the present disclosure provides a table-top sweetener product comprising a composition according to the first form, including any embodiment thereof.

In a third form, the present disclosure provides an edible product comprising a composition according to the first form (including any embodiment thereof).

In a fourth form, the present invention provides the use of a composition according to any one of the three aforementioned forms (including any embodiment thereof) to communicate, enhance or improve the sweetness of an edible product.

In a fifth aspect, the present disclosure provides a method of communicating, enhancing or improving the sweetness of an edible product, comprising: the composition according to any of the first three forms, including any embodiment thereof, is added to an edible product in an amount effective to convey, enhance or improve the sweetness of the edible product.

In a sixth form, the present disclosure provides the use of a composition according to any one of the first three forms (including any embodiment thereof) to communicate, enhance or improve perception of sweetness in a subject in need thereof.

In a seventh form, the present disclosure provides a method of communicating, enhancing or improving perception of sweetness in a subject in need thereof, wherein the method comprises contacting the subject with a composition according to any one of the first three forms (including any embodiment thereof) in an amount effective to communicate, enhance or improve the perception of sweetness by the subject.

In some embodiments of any of the foregoing three morphologies, the amount of tetra-O-methylscutellarein, hexamethoxyquercet, or mixtures thereof effective to convey, enhance, or improve the sweetness of the edible product is from 0.001 to 20 ppm. In some other such embodiments, the amount of tetra-O-methylscutellarein, hexamethoxyquercet, or mixtures thereof effective to convey, enhance, or improve the sweetness of the comestible product is about 2 ppm.

Further aspects and embodiments thereof are set forth in the following detailed description, drawings, abstract, and claims.

Drawings

The following figures are provided to illustrate various embodiments of the compositions and methods disclosed herein. The drawings are provided for illustrative purposes only and are not intended to depict any preferred compositions or preferred methods, nor to be a source of any limitation on the scope of the claimed invention.

FIG. 1 shows a non-limiting example of a typical HPLC chromatogram of polymethoxylated flavones extracted from the distillate residue of orange oil according to the methods described herein and in example 2.

Detailed Description

In the following description, reference is made to specific embodiments which may be practiced, by way of example, with reference to the accompanying drawings. These embodiments are described in detail to enable those skilled in the art to practice the invention described herein, and it is to be understood that other embodiments may be utilized and that logical changes may be made without departing from the scope of the aspects set forth herein. The following description of example embodiments is, therefore, not to be taken in a limiting sense, and the scope of various aspects set forth herein is defined by the appended claims.

The abstract is provided to comply with certain national regulations and to allow the reader to quickly ascertain the nature and gist of the technical disclosure. The Abstract is submitted with the understanding that it will not be used to interpret or limit the scope or meaning of the claims

Polymethoxyflavone

In some forms, polymethoxylated flavones suitable for use in the compositions disclosed herein are tetra-O-methylscutellarein and hexamethoxyquercetn. Such compositions include tetra-O-methyl scutellarein, hexamethoxyquercetn, or any mixture thereof. Note that as used herein in this disclosure, the word "or" is given its broadest reasonable interpretation and should not be construed to have a meaning of "either … … or … …".

As used herein, the term "tetra-O-methyl scutellarein" or "TMS" refers to the compound 5,6,7,4' -tetramethoxyflavone, or a compound having the structure:

as used herein, the term "hexamethoxyquercet" or "HMQ" refers to the compound 3,5,6,7,3',4' -hexamethoxyflavone, or a compound having the structure:

tetra-O-methyl scutellarein, hexamethoxyquercetn or mixtures thereof may be obtained in any suitable manner. For example, they may be isolated from biomass, or alternatively, chemically synthesized or obtained commercially. Non-limiting examples of biomass include the fruit, leaves, stems, bark, and roots of plants.

For example, polymethoxylated flavones may be found in the peel or pulp of Citrus (Citrus) plants. The particular polymethoxylated flavones and their concentrations may vary depending on the particular species of citrus plant. For example, polymethoxylated flavones may be found in the pericarp of certain Citrus species, such as sweet orange (Citrus sinensis), tangerine (Citrus reticulate Blanco) and Citrus (Citrus tangerina). Suitable biomass includes, but is not limited to: sweet orange (Citrus sinensis), tangerine (Citrus reticulate Blanco), mandarin orange (Citrus tenuifolia), Citrus reticulata (Citrus aurantium), kumquat (round kumquat) (Fortunella japonica), ponkan (ponkan) (Citrus deleiosa), satsuma mandarin (unshiu) (Citrus unshiu), Citrus reticulata (Citrus cerementine) (Citrus junmentina), bitter orange (bitter orange) (Citrus aurantium), grapefruit (grapefruit) (Citrus paradisi), dy (Citrus bergamia) (Citrus reticulata), Citrus reticulata (Citrus reticulate), certain species of orange, such as Citrus reticulata, Citrus reticulata (Citrus reticulata), Citrus reticulata (Citrus reticulate) and Citrus reticulata (Citrus reticulata), hybrid Citrus grandis (Citrus reticulata), Citrus grandis (Citrus grandis) (Citrus reticulata), Citrus medica (Citrus reticulata), Citrus reticulata hybrid of Citrus reticulata (Citrus reticulata) and Citrus reticulata (Citrus reticulata), Citrus reticulata (Citrus reticulata), a (Citrus reticulata, a variety of species of a, a (Citrus reticulata, a cornifera, a species of Citrus reticulata, a species of Eupatorium, Citrus reticulata, a, or a, Citrus reticulata, or (cornifera, or a, or a species of, aeroponica grass (Chromolaena odorata), Anabaena caspica (Praxylis clematida), Orthosiphon stamineus (Orthosiphon stamineus), Clerodendrum spicatum (Orthosiphon stamineus), and Charnax fruit (Geofrea decoticans).

In some embodiments, polymethoxylated flavones suitable for use in the compositions provided herein are obtained from PCT publication No. WO 2012/107203.

In some embodiments, tetra-O-methyl scutellarein, hexamethoxyquercetin, or mixtures thereof are purified from the non-volatile residue of orange oil distillation. In some embodiments, tetra-O-methyl scutellarein, hexamethoxyquercetn, or mixtures thereof are purified from orange oil by first extracting orange oil in an aqueous organic solvent, and then separating the extract by chromatography to obtain tetra-O-methyl scutellarein, hexamethoxyquercetn, or mixtures thereof.

Referring to example 1, in one non-limiting embodiment, tetra-O-methyl scutellarein, hexamethoxyquercetn, or a mixture thereof is purified from orange oil extract by a process comprising the steps of:

a. dissolving the distillate residue of orange oil in cyclohexane;

b. to the cyclohexane solution of the distillate residue of orange oil was added an equal volume of methanol to conduct liquid/liquid extraction.

c. Collecting a methanol fraction comprising the defatted distillate residue of orange oil obtained in step (b) and drying the collected methanol fraction;

d. ethyl acetate was added to the collected methanol fraction, and the resulting solution was added to a silica gel column (flash column, 120g, inner diameter 36.6 × x H207);

e. gradient elution was performed by eluting the silica gel column (120g, ID 36.6x H207) first with cyclohexane (2000mL) and then ending with a 1:1 ratio of cyclohexane to ethyl acetate (1500mL), collecting and drying the last two fractions separately;

f. applying the collected penultimate fraction to a preparative C18(2) column and eluting tetra-O-methyl scutellarein and hexamethoxyquercetn; and

g. the collected final fraction was applied to a preparative FPF (2) column and the tetra-O-methyl scutellarein was eluted off.

In some other embodiments thereof, the concentration of the orange oil distillate dissolved in cyclohexane is from 50 to 600g/L, or from 100 to 500g/L, or from 200 to 400 g/L. In some other such embodiments, the concentration of the orange oil distillate dissolved in cyclohexane is about 300g/L, for example 60g of orange oil distillate is dissolved in 200mL of cyclohexane.

In some other embodiments, an amount of ethyl acetate is added to the concentrated methanol fraction. In some embodiments, the v/v ratio of ethyl acetate added to the methanol concentrate ranges from 1:50 to 1:1, or from 1:25 to 1:2, or from 1:15 to 1: 5. In some embodiments, about 15mL of ethyl acetate is added to the concentrated methanol fraction.

In some embodiments, the penultimate fraction comprises tetra-O-methyl scutellarein, hesperetin (tandenetin), hexamethoxyquercetn, and nobiletin (nobiletin). In some embodiments, the yield of the penultimate fraction of tetra-O-methyl scutellarein and hexamethoxyquercetn is 50-99%. In some embodiments, about 2.2g of methoxyflavone product is obtained from 60g of distillate.

In some embodiments, the final fraction comprises tetra-O-methyl scutellarein and nobiletin. In some embodiments, the yield of the final fraction of tetra-O-methylscutellarein and hexamethoxyquercetn is 50-99%. In some embodiments, in some configurations, about 1.8g of methoxyflavone product is obtained from 60g of distillate.

In another embodiment, a mixture of tetra-O-methyl scutellarein and hexamethoxyquercetn is obtained from the distillate residue of orange oil by a process comprising the steps of:

a. dissolving the distillate residue in ethanol;

b. filtering the ethanol solution, and collecting the filtered ethanol solution; and

c. concentrating the filtered ethanol solution to obtain tetra-O-methyl scutellarein and hexamethoxyl quercetn.

In some embodiments thereof, 10g of the distillate of orange oil is dissolved in 990g of ethanol. In some other embodiments, the ethanol is a 50% w/w aqueous solution. In some other embodiments, 100g of the distillate of orange oil is dissolved in 1900g of ethanol. In some such embodiments, the ethanol is a 50% w/w aqueous solution. In some embodiments, the ethanol solution produced in step (a) is filtered through a 0.2 μm PTFE filter.

Referring to example 2 and FIG. 1, in another embodiment, tetra-O-methyl scutellarein, hexamethoxyquercetn or a mixture thereof is purified from orange oil extract by a process comprising the steps of:

a. dissolving the distillate residue of orange oil in ethanol;

b. adding the ethanol solution to a silica gel column;

c. performing gradient elution, namely eluting a silica gel column by using cyclohexane, finishing elution by using cyclohexane to ethanol in a ratio of 4:1, and collecting sub-fractions;

d. applying the collected sub-fractions to a preparative HPLC with a reverse phase column; and

e. eluting polymethoxylated flavones from the reverse phase column.

In some embodiments thereof, 20g of the orange oil distillate is dissolved in 50mL of ethanol. In some other embodiments, the ethanol is a 40% w/w aqueous solution. In some embodiments, the F9, F14, and F15 sub-fractions are collected. In some embodiments, 3,5,6,7,8,3',4' -heptamethoxyflavone and 5,6,7,8,4' -pentamethoxyflavone are purified from the F9 subfractions using an FPF (2) column. In another embodiment, tetra-O-methylscutellarein, hexamethoxyquercetrin, and 5,6,7,8,3',4' -hexamethoxyflavone were purified from the F14 subfraction using a phenomenex C18(2) column. In another embodiment, 5,6,7,3',4' -pentamethoxyflavone is purified from the fraction F15 using an FPF (2) column.

In some embodiments, tetra-O-methyl scutellarein, hexamethoxyquercetin, or mixtures thereof are obtained according to the methods described in PCT publication No. WO 2012/107203.

In some embodiments, tetra-O-methyl scutellarein, hexamethoxyquercetin, or mixtures thereof are synthesized according to the methods described in PCT publication No. WO 2007/083263.

In some embodiments, tetra-O-methyl scutellarein, hexamethoxyquercetin, or mixtures thereof are synthesized according to the methods described in PCT publication No. WO 2011/130705.

In some embodiments, polymethoxylated flavones suitable for use in the compositions provided herein are obtained according to the methods described in PCT publication No. WO 2012/107203.

In some embodiments, polymethoxylated flavones suitable for use in the compositions presented herein are obtained according to the methods described in japanese patent application publication No. JP 2009051738.

In some embodiments, polymethoxylated flavones suitable for use in the compositions set forth herein are obtained according to the methods described in Journal of Agricultural and Food Chemistry (1997), vol.45(2), pp.364-368.

In some forms, polymethoxylated flavones suitable for use in the compositions presented herein are obtained according to the methods described in U.S. patent application publication No. US20150125557a 1.

In some embodiments, polymethoxylated flavones suitable for use in the compositions presented herein are obtained according to the methods described in Essenze, derivanti Agrumari (1993), vol.63(4), pp.395-406.

In some embodiments, polymethoxylated flavones suitable for use in the compositions presented herein are obtained according to the methods described in Molecules (2015), vol.20, pp.20079-20106.

In some embodiments, polymethoxylated flavones suitable for use in the compositions set forth herein are obtained according to the methods described in Journal of Agricultural and Food Chemistry (2012), vol.60(17), pp.4336-4341.

In some embodiments, polymethoxylated flavones suitable for use in the compositions presented herein are obtained according to the methods described in Food Chemistry (2009), vol.119(2), pp.567-572.

In some embodiments, polymethoxylated flavones suitable for use in the compositions presented herein are obtained according to the methods described in Technologies in the Biomedical and Life Sciences (2007), vol.846(1-2), pp.291-297.

In some embodiments, polymethoxylated flavones suitable for use in the compositions set forth herein are obtained according to the methods described in Journal of Agricultural and Food Chemistry (2006), vol.54(12), pp.4176-4185.

In some embodiments, polymethoxylated flavones suitable for use in the compositions presented herein are obtained according to the methods described in Biomedical Chromatography (2006), vol.20(1), pp.133-138.

Composition comprising a metal oxide and a metal oxide

There is a need for alternative (high intensity) sweeteners and sweetness enhancers that are healthy, i.e., non-caloric, non-cariogenic, and ideal for diabetics, as they can also reduce the levels of traditional caloric sweeteners, thus providing less calories than equivalent sweet traditional caloric sweetener palatants. In addition, there is a need for sweetness enhancers that do not contain off-flavors such as bitter or metallic flavors.

As used herein, the term "enhance" refers to the effect on a particular flavor sensation in an edible or other product placed in the oral cavity, which is found to be more pronounced (stronger, enhanced) in taste intensity or which is found to have an earlier developed flavor sensation.

As used herein, the phrase "sweetness enhancer(s)" refers to any compound capable of enhancing or intensifying the perception of sweetness of a sweetener composition or sweetened composition. The phrase "sweetness enhancer" is synonymous with the terms "sweet taste enhancer", "sweetness enhancer" and "sweetness enhancer". As used herein, the phrase "high intensity sweetener(s)" refers to any sweetener, either alone or in combination, in raw, extracted, purified, or any other form, that has a sweetness potency greater than the sweetness of sucrose (regular table sugar), but with relatively little calories. As used herein, the term "sweetener(s)" includes all artificial and natural sweeteners, sugar alcohols (or polyols) and sugar sweeteners (or carbohydrates).

As shown in the examples below, the present disclosure provides a surprising and unexpected discovery that compositions comprising tetra-O-methyl scutellarein, hexamethoxyquercetin, or mixtures thereof, can be used as sweeteners or as sweetness enhancers (e.g., for other natural or artificial sweeteners).

Accordingly, one form of the present disclosure provides a combination comprising tetra-O-methyl scutellarein, hexamethoxyquercetn, or a mixture thereof. In some embodiments thereof, when the composition is added to a 4% w/v sucrose base at a concentration of 0.001 to 20ppm, the sweetness of the 4% w/v sucrose base is enhanced.

In some embodiments, the sweetness of a 4% w/v sucrose base is enhanced when the composition is added to the 4% w/v sucrose base at a concentration of 0.001 to 19 ppm. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 0.001 to 18ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 0.001 to 17ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 0.001 to 16ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 0.001 to 15ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 0.001 to 14ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 0.001 to 13ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 0.001 to 12ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 0.001 to 11ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 0.001 to 10ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 0.001 to 9ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 0.001 to 8ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 0.001 to 7ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 0.001 to 6ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 0.001 to 5ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 0.001 to 4ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 0.001 to 3ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 0.001 to 2ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 0.001 to 1ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, the sweetness of a 4% w/v sucrose base is enhanced when the composition is added to the 4% w/v sucrose base at a concentration of 0.001 to 0.5 ppm. Alternatively, in some embodiments, the sweetness of a 4% w/v sucrose base is enhanced when the composition is added to the 4% w/v sucrose base at a concentration of 0.001 to 0.1 ppm. Alternatively, in some embodiments, the sweetness of a 4% w/v sucrose base is enhanced when the composition is added to the 4% w/v sucrose base at a concentration of 0.001 to 0.05 ppm. Alternatively, in some embodiments, the sweetness of a 4% w/v sucrose base is enhanced when the composition is added to the 4% w/v sucrose base at a concentration of 0.001 to 0.01 ppm. Alternatively, in some embodiments, the sweetness of a 4% w/v sucrose base is enhanced when the composition is added to the 4% w/v sucrose base at a concentration of 0.001 to 0.005 ppm.

Alternatively, in some embodiments, the sweetness of a 4% w/v sucrose base is enhanced when the composition is added to the 4% w/v sucrose base at a concentration of 0.005 to 20 ppm. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 0.01 to 20ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 0.05 to 20ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 0.1 to 20ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 0.5 to 20ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 1 to 20ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 2 to 20ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 3 to 20ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 4 to 20ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 5 to 20ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 6 to 20ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 7 to 20ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 8 to 20ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 9 to 20ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 10 to 20ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 11 to 20ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 12 to 20ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 13 to 20ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 14 to 20ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 15 to 20ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 16 to 20ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 17 to 20ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 18 to 20ppm, the sweetness of the 4% w/v sucrose base is enhanced. Alternatively, in some embodiments, when the composition is added to a 4% w/v sucrose base at a concentration of 19 to 20ppm, the sweetness of the 4% w/v sucrose base is enhanced.

In some embodiments, the sweetness of a 4% w/v sucrose base is enhanced when the composition is added to the 4% w/v sucrose base at a concentration of 0.001ppm, or 0.005ppm, or 0.01ppm, or 0.05ppm, or 0.1ppm, or 0.5ppm, or 1ppm, or 2ppm, or 3ppm, or 4ppm, or 5ppm, or 6ppm, or 7ppm, or 8ppm, or 9ppm, or 10ppm, or 11ppm, or 12ppm, or 13ppm, or 14ppm, or 15ppm, or 16ppm, or 17ppm, or 18ppm, or 19ppm, or 20 ppm.

In some embodiments, the sweetness of a 4% w/v sucrose base is enhanced when the composition is added to the 4% w/v sucrose base at a concentration of 2 ppm.

With respect to sweetness and/or sweetening characteristics, the taste of composition samples according to the several morphologies presented herein can be evaluated in vivo by using a panel of trained sensory evaluators during sweetness estimation, for example using sensory assays such as those described in examples 1 and 2, using a test base comprising a 4% sucrose solution or similar composition.

In sensory studies, panelists are asked to place a sample of the liquid to be evaluated (test substance, e.g., a test base comprising a composition according to several modalities described herein) into the mouth and after a period of time produce a taste perception, the sample is spit out completely. The panelists were then asked to rinse thoroughly with water or black tea to reduce any possible residual effects. Samples can be repeatedly tasted if desired.

Alternatively, the taste of a sample of a composition according to several modalities set forth herein can be evaluated for sweetness and/or sweetening characteristics using the methods described in PCT publication No. WO 2012/107203.

In some embodiments, the composition comprises tetra-O-methyl scutellarein and hexamethoxyquercetn, wherein the ratio of tetra-O-methyl scutellarein to hexamethoxyquercetn is from 1:10 to 25: 1. In some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is from 1:1 to 25: 1. In some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is from 5:1 to 25: 1. In some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 1: 1. Alternatively, in some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 2: 1. Alternatively, in some embodiments, the ratio of tetra-O-methyl scutellarein to hexamethoxyquercetin is 3: 1. Alternatively, in some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 4: 1. Alternatively, in some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 5: 1. Alternatively, in some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 6: 1. Alternatively, in some embodiments, the ratio of tetra-O-methyl scutellarein to hexamethoxyquercetin is 7: 1. Alternatively, in some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 8: 1. Alternatively, in some embodiments, the ratio of tetra-O-methyl scutellarein to hexamethoxyquercetin is 9: 1. Alternatively, in some embodiments, the ratio of tetra-O-methyl scutellarein to hexamethoxyquercetin is 10: 1. Alternatively, in some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 11: 1. Alternatively, in some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 12: 1. Alternatively, in some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 13: 1. Alternatively, in some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 14: 1. Alternatively, in some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 15: 1. Alternatively, in some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 16: 1. Alternatively, in some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 2: 1. Alternatively, in some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 17: 1. Alternatively, in some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 18: 1. Alternatively, in some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 19: 1. Alternatively, in some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 20: 1. Alternatively, in some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 21: 1. Alternatively, in some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 22: 1. Alternatively, in some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 23: 1. Alternatively, in some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 24: 1. Alternatively, in some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 25: 1.

In some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 1: 2. Alternatively, in some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 1: 3. Alternatively, in some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 1: 4. Alternatively, in some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 1: 5. Alternatively, in some embodiments, the ratio of tetra-O-methyl scutellarein to hexamethoxyquercetin is 1: 6. Alternatively, in some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 1: 7. Alternatively, in some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 1: 8. Alternatively, in some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 1: 9. Alternatively, in some embodiments, the ratio of tetra-O-methylscutellarein to hexamethoxyquercetin is 1: 10.

In some embodiments, the composition comprises tetra-O-methyl scutellarein, hexamethoxyquercetn, or mixtures thereof in a purity of greater than about 60% by weight, such as greater than about 70% by weight, greater than about 80% by weight, greater than about 90% by weight, greater than about 98% by weight, or greater than about 99% by weight.

The composition can provide a sweetness comparable to one to three teaspoons of granulated sugar, or a sweetness comparable to two teaspoons of granulated sugar. For example, the composition may comprise a sweetness comparable to granulated sugar (sucrose) and may therefore be used in a "spoon-to-spoon" or "cup-to-cup" manner instead of sugar. As used herein, the phrase "a sweetness comparable to … …" refers to an experienced sensory evaluator determining, on average, the sweetness exhibited in the first composition to be in the range of 80% to 120% of the sweetness exhibited in the second composition. The phrase "a sweetness comparable to … …" relates to a determination made by four or more experienced sensory evaluators in a sweetness matching test (hereinafter referred to as "taste and saliva analysis") as described below. Thus, for example, if the sweetness of a sweetener composition according to the morphology presented herein falls within the range of sweetness exhibited by 80-120 mg/mL of sucrose, then 100mg/mL of a sweetener composition according to the morphology presented herein may provide a sweetness comparable to that of 100mg/mL of sucrose.

In some embodiments, the composition further comprises at least one additional sweetener. The at least one additional sweetener may be an artificial sweetener, or a natural sweetener.

Any suitable additional sweetener may be included in the composition. For example, in some embodiments, the at least one additional sweetener is selected from the group consisting of: albizzia julibrissin (abriasaponin), abrin triterpenoids (abrusoside) (especially abrin A, abrin B, abrin C, abrin D), acesulfame potassium, Edwardsien (advantame), Albizzia julibrissin (albicasaponin), alitame, aspartame, super-aspartame, cloudbursin (bayunosides) (especially cloudbursin 1, cloudbursin 2), brazzein (brezzein), bryoside, bryonoside, bryodulcoside, fleshy hemsleyasaponin (cardosiloside), carrelame, curculin, anthocyanin (cyclinin), chlorogenic acid, cyclamate and salts thereof, cyclocaryophylloside I (cyclocaryophyllide I), dihydrodihydronuclein-3-acetate, dihydronuclein, dulcoside (dulcoside), glycyrrhizin (mangostimulin V), isoquercitrin (isoquercitrin, isoquercitrin V), n- (4-cyanophenyl) -N- (2, 3-methylenedioxybenzyl) guanidineacetic acid (lugduname), magap, mabinlin (mabinlins), miraculin (micculin), mogrosides (Lo Han Guo) (in particular mogroside IV and mogroside V), monatin and its derivatives, monellin (monellin), sapindoside, naringin dihydrochalcone (NarDHC), Neohesperidin Dihydrochalcone (NDHC), neotame, Osladin (ostramin), pentadin (pentadin), brasilipin I-V, perillartine (perillartine), D-phenylalanine, phlomisoside (phssoside), in particular phloroside 1, phloroside 2, phloridin 3, phloridin 4, phloridin (phyllodulin), polidopins (polidopides), in particular polidoposidine A (polidophyllin A), in (polidophyllin A) (in particular), (polidophyllin A), (polidocosaponin A), (polidocusarin, and D-, Rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside G, rebaudioside H, rebaudioside M), rubusoside, saccharin and its salts and derivatives, gynura segetum hemsleyadin (scandenside), selliguenin A, siamenosides (particularly siamenoside I), stevia rebaudiana, steviolbioside, stevioside and other steviosides, malacylins (strigines), particularly malacylins 1, malacylins 2, malacylins 4, rubusoside A (suavioside A), rubusoside B, rubusoside G, rubusoside H, rubusoside I, rubusoside J, sucralose, sucronate, sucrooctate, thaumatin (talin), lewisoside A15, thaumatin (thaumatin), particularly amauroside I, sinensetin and trans-anisaldehyde, trilobatin, D-tryptophan, erythritol, galactitol, hydrogenated starch syrups (including maltitol syrup and sorbitol syrup), inositol, isomalt (isomalt), lactitol, maltitol, mannitol, xylitol, arabinose, dextrin, dextrose, fructose, high fructose corn syrup, fructo-oligosaccharides syrup, galactose, galacto-oligosaccharides, glucose and (hydrogenated) starch syrups/hydrolysates, isomaltulose (isomaltulose), lactose, hydrolyzed lactose, maltose, mannose, rhamnose, ribose, sucrose, tagatose, trehalose and xylose.

In some other embodiments of any of the above embodiments, the at least one additional sweetener is selected from the sweeteners disclosed in PCT publication No. WO 2012/107203.

Alternatively, in some other embodiments of any of the above embodiments, the at least one additional sweetener is selected from the compounds disclosed in PCT publication No. WO 2011/130705.

Alternatively, in some other embodiments of any of the above embodiments, the at least one additional sweetener is selected from the compounds disclosed in european patent No. 0605261B 1.

Alternatively, in some other embodiments of any of the above embodiments, the at least one additional sweetener is a polymethoxylated flavone selected from the group consisting of: nobiletin (nobiletin), sinenstein (sinenstein), heptamethoxyflavone and tangeretin (tandenetin).

Alternatively, in some other embodiments of any of the above embodiments, the at least one additional sweetener is a polymethoxylated flavone as disclosed in PCT publication No. WO 2012/107203.

Alternatively, in some other embodiments of any of the above embodiments, the at least one additional sweetener is a polymethoxylated flavone as disclosed in PCT publication No. WO 2011/130705.

Alternatively, in some other embodiments of any of the above embodiments, the at least one additional sweetener is a polymethoxylated flavone as disclosed in european patent No. 0605261B 1.

As used herein, the term "nobiletin" or "NOB" refers to the compound 5,6,7,8,3',4' -hexamethoxyflavone or a compound having the structure:

as used herein, the term "sinenstein" or "SIN" refers to the compound 5,6,7,3',4' -pentamethoxyflavone or a compound having the structure:

as used herein, the term "heptamethoxyflavone" or "HMF" refers to the compound 3,5,6,7,8,3',4' -heptamethoxyflavone or a compound having the structure:

as used herein, the term "orange" or "TAN" refers to a compound

5,6,7,8,4' -pentamethoxyflavone or a compound having the following structure:

in some embodiments, the composition further comprises at least one additional sweetness enhancer, or in some additional embodiments, at least two or at least three additional sweetness enhancers. Suitable additional sweetness enhancers are well known in the art. In some embodiments, the at least one additional sweetness enhancer is selected from the group consisting of: terpenes (e.g., sesquiterpenes, diterpenes and triterpenes), flavonoids, amino acids, proteins, polyols, other known natural sweeteners (e.g., cinnamaldehydes, selligueians, and hematoxylin), secodammarane glycosides (secodammaranes) and analogs thereof. Exemplary sweetness enhancers include steviol glycosides, such as stevioside, steviolbioside, rebaudioside a, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, dulcoside a, rubusoside, glycyrrhizin (hernandulcin), rosinditerpene, sapindoside, sinsenoside (baiyunoside), phlomisoside (phlomisoside) such as phlomisoside I and phlomisoside II; glycyrrhizic acid; brassinoglycyrrhizins such as brassinoglycyrrhizin I, brassinoglycyrrhizin II, brassinoglycyrrhizin III, and brassinoglycyrrhizin IV; osscoreopsis glabra, polypodosides (polypodosides), such as polypodoside a and polypodoside B; mogrosides such as mogroside IV and mogroside V; abrin A or abrin B; cyclocarioside (cycloariosides), such as cyclocarioside a and cyclocarioside B; pterocarcoside A and pterocarcoside B; flavonoids such as phyllodulcin, phlorizin, neoastilbin (neoastilbin), and dihydroquercetin acetate; amino acids such as glycine and monatin; proteins, such as thaumatin (thaumatin I, thaumatin II, thaumatin III, and thaumatin IV), monellin, mabinlin (mabinlin I and mabinlin II), brazzein, miraculin (miraculin), and curculin; polyols, such as erythritol; cinnamic aldehyde; pteridopterin, e.g., pteridopterin a and pteridopterin B; hematoxylin; and mixtures thereof. Additional exemplary sweetness enhancers include rosin diterpenes; phlorizin; new astilbin; dihydroquercetin acetate; glycine; erythritol; cinnamic aldehyde; pteridophytin A; pteridophytin B; hematoxylin; rebaudioside a; rebaudioside B; rebaudioside C; rebaudioside D; rebaudioside E; dulcoside a; steviolbioside; rubusoside (rebaudioside A); stevia rebaudiana (Bertoni) Hemsl; stevioside; steviol 13-O-beta-D-glucoside; mogroside V; momordica grosvenori; siamenoside; siamenoside I; monatin and its salts (monatin SS, RR, RS, SR); curculin; glycyrrhizic acid and its salts; thaumatin I; thaumatin II; thaumatin III; thaumatin IV; monellin; capelin I; capelin II; blazidine; glycyrrhizin; a phyllodulcin; sarsasaponin (glycophyllin); phlorizin; trilobatin; white stichoposide; ostrin Gum of Eupatorium; polybodorside a; polybodorside B; pterocarcoside A; pterocarcoside B; soapberry sesquiterpene glycosides; soapberry sesquiterpene glycosides lib; phlomisoside I; phlomisoside II; glycyrrhizin I from Brazil; glycyrrhizin II from Brazil; glycyrrhizin III from Brazil; glycyrrhizin VI from brazil; glycyrrhizin V from brazil; cyclocarya paliurus glycoside A; cyclocarya paliurus glycoside B; rubusoside A; rubusoside B; rubusoside G; rubusoside H; rubusoside I; rubusoside J; labdane glucosides (labdane glycosides); white stichoposide; gaudichhaudioside A; mogroside IV; isomogroside; isobryonia root sweet glycosides (bryodulcoside); bryobioside; bryoside; bryoside; fleshy hemsleyasaponin V; fleshy hemsleyasaponin VI; cang notoginseng hemsleyaside R6; 11-oxomogroside V; abrin triterpenoid A; abrin triterpene glycoside B; abrin triterpene glycoside C; abrin triterpene glycoside D; abrin E; esculin XX; glycyrrhizin; 3-apioglycyrrhizin (glycyrrhetin); 3-arabinoglucuronoside glycyrrhetinate (araboglycyrrhizin); pantoprazole; perillaldehyde (perillaldehyde); rebaudioside F; steviol; 13- [ (2-O- (3-O- α -D-glucopyranosyl) - β -D-glucopyranosyl-3-O- β -D-glucopyranosyl) oxy ] kauri-16-en-18-oic acid β -D-glucopyranosyl ester; 13- [ (2-O- β -D-glucopyranosyl-3-O- (4-O- α -D-glucopyranosyl) - β -D-glucopyranosyl) oxy ] kauri-16-en-18-oic acid β -D-glucopyranosyl ester; 13- [ (3-O- β -D-glucopyranosyl) oxy ] kauri-16-ene-18-oic acid β -D-glucopyranosyl ester; 13-hydroxy-kauri-16-en-18-oic acid beta-D-glucopyranosyl ester; 13-methyl-16-oxo-17-norkauran-18-oic acid β -D-glucopyranosyl ester; 13- [ (2-O- β -D-glucopyranosyl-3-O- β -D-glucosylglucosyl- β -D-glucopyranosyl) oxy ] kauri-15-en-18-oic acid β -D-glucopyranosyl ester; 13- [ (2-O-D-glucopyranosyl-3-O-D-glucopyranosyl- β -D-glucopyranosyl) oxy ] kauri-15-en-18-oic acid; 13- [ (2-O- β -D-glucopyranosyl-3-O- β -D-glucopyranosyl ] - β -D-glucopyranosyl) oxy ] -17-hydroxy-kauri-15-en-18-oic acid β -D-glucopyranosyl ester; 13- [ (2-O- β -D-glucopyranosyl-3-O-D-glucopyranosyl- β -D-glucopyranosyl) oxy ] -16-hydroxykaurane-18-oic acid β -D-glucopyranosyl ester; 13- [ (2-O- β -D-glucopyranosyl-3-O- β -D-glucopyranosyl) oxy ] -16-hydroxykaurane-18-acid; isosteviol; mogroside IA; mogroside IE; mogroside 11-A; mogroside 11-E; mogroside III; mogroside V; isomogroside V; 11-oxomogroside; mogrol; 11-oxo-mogrol; 11-oxomogroside IA; 1- [ 13-hydroxykauri-16-en-18-oate ] β -D-glucopyranosuronic acid; 13- [ (2-O- β -D-glucopyranosyl) oxy ] -17-hydroxy-kauri-15-en-18-oic acid β -D-glucopyranosyl ester; 13- [ (2-O- β -D-glucopyranosyl) oxy ] kauri-16-ene-18-oic acid- (2-O- β -D-glucopyranosyl) ester (rebaudioside E); 13- [ (2-O- α -L-rhamnosyl-3-O- β -D-glucopyranosyl) oxy ] kauri-16-ene-18-oic acid- (2-O- β -D-glucopyranosyl) ester; 13- [ (2-O- β -D-glucopyranosyl-3-O-P-D-glucopyranosyl) oxy ] -dammara-16-ene-18-oic acid- (2-O-a-L-rhamnosyl- β -D-glucopyranosyl) ester; 13- [ (2-O- β -D-glucopyranosyl) oxy ] -17-oxo-kauri-15-enoic acid β -D-glucopyranosyl ester; 13- [ (2-O- (6-O- β -D-glucopyranosyl) - β -D-glucopyranosyl) oxy ] kauri-16-en-18-oic acid β -D-glucopyranosyl ester; 13- [ (2-O- β -D-glucopyranosyl-3-O- β -D-fructofuranosyl- β -D-glucopyranosyl) oxy ] kauri-16-en-18-oic acid β -D-glucopyranosyl ester; 13- [ (2-O- β -D-glucopyranosyl) oxy ] kauri-16-ene-18-oic acid- (6-O- β -D-xylopyranosyl- β -D-glucopyranosyl) ester; 13- [ (2-O- β -D-glucopyranosyl) oxy ] kauri-16-ene-18-oic acid- (4-O- (2-O- α -D-glucopyranosyl) - α -D-glucopyranosyl) ester; 13- [ (2-O- β -D-glucopyranosyl-3-O-P-D-glucopyranosyl- β -D-glucopyranosyl) oxy ] kauri-16-ene-18-oic acid- (2-O-6-deoxy- β -D-glucopyranosyl) ester; 13- [ (2-O- β -D-glucopyranosyl) oxy ] kauri-15-ene-18-oic acid β -D-glucopyranosyl ester; 13- [ (2-O- β -D-glucopyranosyl-3-O- β -D-xylopyranosyl-P-D-glucopyranosyl) oxy ] kauri-16-en-18-oic acid β -D-glucopyranosyl ester; 13- [ (2-O- β -D-xylopyranosyl- β -D-glucopyranosyl) oxy ] kauri-16-ene-18-oic acid β -D-glucopyranosyl ester; 13- [ (3-O- β -D-glucopyranosyl) oxy ] kauri-16-ene-18-oic acid P-D-glucopyranosyl ester; 13- [ (2-O-6-deoxy- β -D-glucopyranosyl-3-O- β -D-glucopyranosyl) oxy ] kauri-16-en-18-oic acid β -D-glucopyranosyl ester; 13- [ (2-O-6-deoxy β -D-glucopyranosyl- β -D-glucopyranosyl) oxy ] kauri-16-ene-18-oic acid β -D-glucopyranosyl ester; and mixtures thereof.

In some other embodiments, the one or more additional sweetness enhancers comprise rebaudioside C, rebaudioside F, rebaudioside D, 13- [ (2-O- β -D-glucopyranosyl-3-O- β -D-glucopyranosyl ] - β -D-glucopyranosyl) oxy ] -17-hydroxy-kauri-15-ene-18-oic acid β -D-glucopyranosyl ester, 13- [ (2-O- (3-O- β -D-glucopyranosyl) - β -D-glucopyranosyl-3-O- β -D-glucopyranosyl) oxy ] kauri-16-ene-18-oic acid β - D-glucopyranosyl ester, and rubusoside. . In some other embodiments, the at least one sweetness enhancer is rebaudioside a, steviol glycoside, rebaudioside D, rebaudioside E, mogroside V, mogroside IV, brazzein, and monatin.

In some embodiments, the at least one sweetness enhancer is present in an amount at or below the sweetness detection threshold level for the at least one sweetness enhancer. In some embodiments, the at least one sweetness enhancer is present in an amount below the sweetness detection threshold level of the at least one sweetness enhancer. The sweetness detection threshold level may be specific to a particular compound. Typically, however, in some embodiments, the at least one sweetness enhancer is present in an amount ranging from 0.5ppm to 1000 ppm. For example, the at least one sweetness enhancer is present in an amount ranging from 1ppm to 300 ppm; or the at least one sweetness enhancer is present in an amount ranging from 0.1ppm to 75 ppm; or the at least one sweetness enhancer is present in an amount ranging from 500ppm to 3,000 ppm.

As used herein, the terms "sweetness threshold", "sweetness recognition threshold" and "sweetness detection threshold" are understood to refer to the level of the lowest known concentration of a certain sweet compound that is perceptible to the human taste perception, and which may vary from person to person. For example, a typical sweetness threshold level of sucrose in water may be 0.5%. For further example, at least one sweetness enhancer used in water at least 25% lower and at least 25% higher than the sucrose detection level of at least 0.5% can be assayed in water to determine a sweetness threshold level. One skilled in the art will be able to select the concentration of the at least one sweetness enhancer such that enhanced sweetness may be imparted to a composition comprising the at least one sweetener. For example, the skilled person may select the concentration of the at least one sweetness enhancer such that the at least one sweetness enhancer does not impart any perceptible sweetness to a composition that does not comprise the at least one sweetener. In some embodiments, the compounds listed above as sweeteners may also be used as sweetness enhancers. In general, certain sweeteners may also be used as sweetness enhancers and vice versa.

Preparation

In some forms, the present disclosure provides formulations comprising a composition according to the foregoing forms and embodiments thereof. In these formulations, such compositions may take any suitable form, including but not limited to amorphous solids, crystalline solids, powders, tablets, liquids, cubes, frostings or glazes, granulated products, encapsulated forms surrounding or coated on carriers/particles, wet or dry, or combinations thereof.

For example, in some embodiments, the formulation is provided in a pre-dispensed package or ready-to-use formulation comprising a composition comprising: tetra-O-methyl scutellarein, hexa-methoxy quercetn or a mixture thereof. For example, in one such embodiment, a single serving of the packaged formulation (typically about a1 gram portion) provides a sweetness comparable to that contained in two teaspoons of granulated sugar (sucrose). It is known in the art that a "teaspoon" of sucrose contains about 4 grams of sucrose.

In some other embodiments, a volume of the ready-to-use formulation may provide a sweetness comparable to the same volume of granulated sugar. For example, a single-serving composition comprising tetra-O-methylscutellarein, hexamethoxyquercet, or a mixture thereof (e.g., 1 gram) may provide a sweetness equivalent to about 0.9 to about 9.0 grams of granulated sugar (sucrose). In another form, 1 gram of a composition according to several forms presented herein contains less calories (calories) and carbohydrates compared to about 1 gram of granulated sugar, e.g., more than 10% less calories, or more than 20% less calories, or more than 30% less calories, or more than 40% less calories, or more than 50% less calories, or more than 60% less calories, or more than 70% less calories, or more than 80% less calories, or more than 90% less calories.

The formulations provided herein may contain other additives known to those skilled in the art. Such additives include, but are not limited to, foaming agents, fillers, carriers, fibers, sugar alcohols, oligosaccharides, sugars, high intensity sweeteners, nutritive sweeteners, flavoring agents, flavor enhancers, flavor stabilizers, acidulants, anti-caking agents, free-flowing agents, and the like. Such additives are described, for example, in h.mitchell, sweenters and sun alternations in Food Technology (2006), which is incorporated herein by reference in its entirety. As used herein, the term "flavoring agent" includes those flavoring agents known to the skilled artisan, such as natural and artificial flavoring agents. These flavouring agents may be selected from synthetic flavouring oils and flavouring aromatic substances or oils from plants, leaves, flowers, fruits etc., oleoresins and extracts, and combinations thereof. Non-limiting flavoring oils include spearmint oil, cinnamon oil, oil of wintergreen (methyl salicylate), peppermint oil, clove oil, bay oil, anise oil, eucalyptus oil, thyme oil, cedar leaf oil, oil of nutmeg, allspice, oil of sage, nutmeg (mace), oil of bitter almonds, and cassia oil. Also useful are artificial, natural and synthetic fruit flavors such as vanilla, and citrus oil including lemon, orange, lime, grapefruit, japanese pomelo (yazu), tangerine (sudachi), and fruit essences including apple, pear, peach, grape, blueberry, strawberry, raspberry, cherry, plum, pineapple, watermelon, apricot, banana, melon, apricot, plum, cherry, raspberry, blackberry, tropical fruit, mango, mangosteen, pomegranate, papaya, and the like. Other potential flavoring agents include milk flavoring, butter flavoring, cheese flavoring, cream flavoring, and yogurt flavoring; a vanilla flavoring; tea or coffee flavors, such as green tea flavor, oolong tea flavor, cocoa flavor, chocolate flavor and coffee flavor; mint flavors, such as peppermint flavor, spearmint flavor and japanese mint flavor; spice flavors such as asafetida flavor, indian caraway flavor, anise flavor, angelica flavor, fennel flavor, allspice flavor, cinnamon flavor, chamomile flavor, mustard flavor, cardamom flavor, caraway flavor, fennel flavor, clove flavor, pepper flavor, coriander flavor, sassafras flavor, salty flavor, zanthoxylum flavor, perilla flavor, juniper berry flavor, ginger flavor, star anise flavor, horseradish flavor, thyme flavor, tarragon flavor, dill flavor, capsicum flavor, nutmeg flavor, basil flavor, marjoram flavor, rosemary flavor, bay leaf flavor, and mustard (japanese horseradish) flavor; wine flavors such as red wine flavor, whisky flavor, brandy flavor, rum flavor, gin flavor and liqueur flavor; a floral flavoring agent; and vegetable flavors such as onion flavor, garlic flavor, cabbage flavor, carrot flavor, celery flavor, mushroom flavor, and tomato flavor. These flavoring agents may be used in liquid or solid form, and may be used alone or in admixture. Commonly used flavors include mints such as peppermint, menthol, spearmint, artificial vanilla, cinnamon derivatives and various fruit flavors, whether employed individually or in admixture. Flavors may also provide breath freshening properties, particularly mint flavors when used in combination with cooling agents.

Flavors may also provide breath freshening properties, particularly mint flavors when used in combination with cooling agents. These flavoring agents may be used in liquid or solid form, and may be used alone or in admixture. Other useful flavoring agents include aldehydes and esters such as cinnamyl acetate, cinnamaldehyde, citral diethyl acetal, dihydrocarvyl acetate, eugenyl formate, p-methylanisole, and the like. In general, any flavoring agent or Food additive may be Used, such as those described by the National Academy of Sciences in Food Processing, publication 1274, pages 63-258, by Chemicals Used. This publication is incorporated herein by reference.

In some embodiments, an aldehyde flavoring agent is also included. Other examples of aldehyde flavors include, but are not limited to, acetaldehyde (apple), benzaldehyde (cherry, almond), anisaldehyde (licorice, anise), cinnamaldehyde (cinnamon), citral, i.e., α -citral (lemon, lime), neral, i.e., β -citral (lemon, lime), decanal (orange, lemon), ethyl vanillin (vanilla, cream), heliotropin, i.e., piperonal (vanilla, cream), vanillin (vanilla, cream), α -amyl cinnamic aldehyde (pungent fruit flavor), butyraldehyde (butter, cheese), valeraldehyde (butter, cheese), citronellal (modified product, various types), decanal (citrus fruit), aldehyde C-8 (citrus fruit), aldehyde C-9 (citrus fruit)), aldehyde C-12 (citrus fruit), 2-ethyl butyraldehyde (berry), hexenal, i.e., trans-2 (berries), tolyl aldehyde (cherry, almond), veratraldehyde (vanilla), 2, 6-dimethyl-5-heptene, i.e., melonal (melon), 2, 6-dimethyloctanal (green fruit) and 2-dodecenal (citrus, orange), cherry, grape, strawberry shortcakes and mixtures thereof. These lists of flavoring agents are exemplary only and are not meant to generally limit the scope of the disclosure or the term "flavoring agent".

In some embodiments, the flavoring agent may be used in liquid form or in dry form. When used in the latter form, suitable drying means may be used, for example spray drying the oil. Alternatively, the flavoring agent may be absorbed onto a water-soluble material, such as cellulose, starch, sugar, maltodextrin, gum arabic, and the like, and in some other embodiments, encapsulated. Techniques for preparing such dry forms are well known.

In some embodiments, flavoring agents are used in many different physical forms well known in the art to provide an initial burst of flavor or a prolonged flavor sensation. Without being limited thereto, these physical forms include free forms such as spray-dried, powdered, beaded forms, encapsulated forms and mixtures thereof.

In some forms, the present disclosure provides a tabletop sweetener product comprising a composition according to a final embodiment of the foregoing forms.

As used herein, the term "tabletop sweetener" refers to a sweetener composition comprising at least one sweetener and optionally at least one sweetness enhancer, which can be used to prepare various food products or as an additive to food products. As an example, tabletop sweeteners may be used to prepare baked goods or other sweetened foods. As another example, tabletop sweeteners may be used to flavor, sweeten, or otherwise customize prepared food products, such as beverages, fruits, or yogurt.

In some embodiments, the tabletop sweetener is in crystalline, granular or powder form. In some embodiments, the tabletop sweeteners comprise one or more sweeteners or one or more sweetness enhancers. In a particular embodiment, the tabletop sweeteners include one or both of a caloric sweetener or a substantially non-caloric sweetener, and, in some cases, one or more sweetness enhancers. Typical examples of caloric sweeteners that may be used in tabletop sweeteners include sucrose, fructose, and glucose. Common table top forms of these caloric sweeteners include sucrose, honey, and the like. For the last decades, substantially calorie-free sweeteners have become popular. In many instances, these sweeteners may be used as substitutes for caloric sweeteners, commonly referred to as "sugar substitutes.

Exemplary tabletop sweetener products that can be used are described above and are additionally disclosed in PCT publication No. WO 2012/107203.

In some embodiments, the tabletop sweetener product comprises an effective amount of a composition comprising tetra-O-methyl scutellarein, hexamethoxyquercetn, or a mixture thereof.

In some forms, the present disclosure provides an edible product comprising a composition according to the foregoing forms and embodiments thereof. In some embodiments, the edible product comprises an effective amount of a composition comprising tetra-O-methyl scutellarein, hexamethoxyquercetn, or mixtures thereof.

In some embodiments, the effective amount ranges from 0.001 to 19 ppm. Alternatively, in some embodiments, the effective amount ranges from 0.001 to 18 ppm. Alternatively, in some embodiments, the effective amount ranges from 0.001 to 17 ppm. Alternatively, in some embodiments, the effective amount ranges from 0.001 to 16 ppm. Alternatively, in some embodiments, the effective amount ranges from 0.001 to 15 ppm. Alternatively, in some embodiments, the effective amount ranges from 0.001 to 14 ppm. Alternatively, in some embodiments, the effective amount ranges from 0.001 to 13 ppm. Alternatively, in some embodiments, the effective amount ranges from 0.001 to 12 ppm. Alternatively, in some embodiments, the effective amount ranges from 0.001 to 11 ppm. Alternatively, in some embodiments, the effective amount ranges from 0.001 to 10 ppm. Alternatively, in some embodiments, the effective amount ranges from 0.001 to 9 ppm. Alternatively, in some embodiments, the effective amount ranges from 0.001 to 8 ppm. Alternatively, in some embodiments, the effective amount ranges from 0.001 to 7 ppm. Alternatively, in some embodiments, the effective amount ranges from 0.001 to 6 ppm. Alternatively, in some embodiments, the effective amount ranges from 0.001 to 5 ppm. Alternatively, in some embodiments, the effective amount ranges from 0.001 to 4 ppm. Alternatively, in some embodiments, the effective amount ranges from 0.001 to 3 ppm. Alternatively, in some embodiments, the effective amount ranges from 0.001 to 2 ppm. Alternatively, in some embodiments, the effective amount ranges from 0.001 to 1 ppm. Alternatively, in some embodiments, the effective amount ranges from 0.001 to 0.5 ppm. Alternatively, in some embodiments, the effective amount ranges from 0.001 to 0.1 ppm. Alternatively, in some embodiments, the effective amount ranges from 0.001 to 0.05 ppm. Alternatively, in some embodiments, the effective amount ranges from 0.001 to 0.01 ppm. Alternatively, in some embodiments, the effective amount ranges from 0.001 to 0.005 ppm.

Alternatively, in some embodiments, the effective amount ranges from 0.005 to 20 ppm. Alternatively, in some embodiments, the effective amount ranges from 0.01 to 20 ppm. Alternatively, in some embodiments, the effective amount ranges from 0.05 to 20 ppm. Alternatively, in some embodiments, the effective amount ranges from 0.1 to 20 ppm. Alternatively, in some embodiments, the effective amount ranges from 0.5 to 20 ppm. Alternatively, in some embodiments, the effective amount ranges from 1 to 20 ppm. Alternatively, in some embodiments, the effective amount ranges from 2 to 20 ppm. Alternatively, in some embodiments, the effective amount ranges from 3 to 20 ppm. Alternatively, in some embodiments, the effective amount ranges from 4 to 20 ppm. Alternatively, in some embodiments, the effective amount ranges from 5 to 20 ppm. Alternatively, in some embodiments, the effective amount ranges from 6 to 20 ppm. Alternatively, in some embodiments, the effective amount ranges from 7 to 20 ppm. Alternatively, in some embodiments, the effective amount ranges from 8 to 20 ppm. Alternatively, in some embodiments, the effective amount ranges from 9 to 20 ppm. Alternatively, in some embodiments, the effective amount ranges from 10 to 20 ppm. Alternatively, in some embodiments, the effective amount ranges from 11 to 20 ppm. Alternatively, in some embodiments, the effective amount ranges from 12 to 20 ppm. Alternatively, in some embodiments, the effective amount ranges from 13 to 20 ppm. Alternatively, in some embodiments, the effective amount ranges from 14 to 20 ppm. Alternatively, in some embodiments, the effective amount ranges from 15 to 20 ppm. Alternatively, in some embodiments, the effective amount ranges from 16 to 20 ppm. Alternatively, in some embodiments, the effective amount ranges from 17 to 20 ppm. Alternatively, in some embodiments, the effective amount ranges from 18 to 20 ppm. Alternatively, in some embodiments, the effective amount ranges from 19 to 20 ppm.

In some embodiments, the effective amount is 0.001ppm, or 0.005ppm, or 0.01ppm, or 0.05ppm, or 0.1ppm, or 0.5ppm, or 1ppm, or 2ppm, or 3ppm, or 4ppm, or 5ppm, or 6ppm, or 7ppm, or 8ppm, or 9ppm, or 10ppm, or 11ppm, or 12ppm, or 13ppm, or 14ppm, or 15ppm, or 16ppm, or 17ppm, or 18ppm, or 19ppm, or 20 ppm.

Edible products include, but are not limited to, beverages, dental products, cosmetics, pharmaceuticals and animal feeds or animal foods. For example, edible products include all food products including, but not limited to, cereal products, rice products, tapioca products, sago products, bakery products, biscuit products, pastry products, bread products, confectionery products, gummy candies, chewing gums, chocolates, frostings, honey products, molasses products, yeast products, baking powders, salt and spice products, savory products, mustard products, vinegar products, sauces (dressings), tobacco products, cigars, cigarettes, processed foods, cooked fruit and vegetable products, meat and meat products, jellies, jams, purees, egg products, milk and dairy products, yogurt, cheese products, butter and butter substitute products, milk substitute products, soy products, edible oil and fat products, pharmaceuticals, beverages, carbonated beverages, alcoholic beverages, beer, soft drinks, mineral water and aerated water and other non-alcoholic beverages, fruit drinks, juices, coffee, artificial coffee, tea, cocoa, including forms requiring reconstitution, food extracts, plant extracts, meat extracts, flavorings, sweeteners, nutraceuticals, gelatin, pharmaceutical and non-pharmaceutical gums, tablets, lozenges, drops, emulsions, elixirs, syrups and other preparations for preparing beverages, and combinations thereof.

The term "non-alcoholic beverage" as used herein includes, but is not limited to, all non-alcoholic beverages referred to in the sweetener for food products under the directive 2003/115/EC # 12/22/2003 and directive 94/35/EC # 30/6/2004, which are incorporated herein by reference. Non-limiting examples include water-based flavored beverages, low-energy or no sugar added, milk and milk derivatives or fruit juice-based beverages, low-energy or no sugar added nonalcoholic beverages, Gaseosa: a nonalcoholic water beverage is prepared by adding carbon dioxide, sweetener and flavoring agent.

Edible products include, but are not limited to, water-based edible products, solid dry-based edible products, dairy-derived products, and dairy substitute products. In one form, the edible product is a water-based edible product, including, but not limited to, beverages, water, aqueous beverages, sweetened/slightly sweetened water beverages, flavored carbonated and sparkless mineral waters and drinking waters, carbonated beverages, non-carbonated beverages, carbonated waters, sparkless waters, soft drinks, non-alcoholic beverages, beer, wine, white spirits, fruit beverages, juices, fruit juices, vegetable juices, bouillon beverages, coffee, tea, black tea, green tea, oolong tea, herbal infusions, cocoa (e.g., waters), tea beverages, coffee beverages, cocoa beverages, infusions, syrups, frozen fruits, frozen fruit juices, water-based ices, fruit ices, sorbets, condiments, salad dressings, jams, orange sauces, canned fruits, savory foods, deli products, such as deli salads, sauces, tomato sauces, mustard sauces, pickles and pickled fish, pickles, and salted fish, Sauces, soups, and beverage plant materials (e.g., whole or ground), or instant powders for reconstitution (e.g., coffee beans, ground coffee, instant coffee, cocoa beans, cocoa powder, instant cocoa, tea leaves, instant tea powder). In another embodiment, the comestible product is a solid dry comestible product including, but not limited to, cereals, baked goods, cookies, bread, breakfast cereals, cereal bars, energy/nutritional bars, granola, cakes, rice cakes, soft biscuits, hard biscuits, donuts, muffins, pastries, candies, chewing gums, chocolate products, chocolate, fondant, hard candies, marshmallows, pressed tablets, snack foods, plant materials (whole or ground), and instant powders for reconstitution.

Illustrative edible products are also disclosed in PCT publication No. WO 2012/107203.

Method and use

In certain forms, the present disclosure provides the use of a composition according to the foregoing forms and embodiments to communicate, enhance or improve the sweetness of an edible product.

In some embodiments thereof, the present disclosure provides a method of communicating, enhancing or improving the sweetness of an edible product comprising the steps of: the composition according to any of the foregoing aspects and embodiments is added to an edible product in an amount effective to convey, enhance or improve the sweetness of the edible product.

In some embodiments, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 0.001 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 0.001 to 19 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 0.001 to 18 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 0.001 to 17 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 0.001 to 16 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 0.001 to 15 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 0.001 to 14 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 0.001 to 13 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 0.001 to 12 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 0.001 to 11 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 0.001 to 10 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 0.001 to 9 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 0.001 to 8 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 0.001 to 7 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 0.001 to 6 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 0.001 to 5 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 0.001 to 4 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 0.001 to 3 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 0.001 to 2 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 0.001 to 1 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 0.001 to 0.5 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 0.001 to 0.01 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the edible product is from 0.001 to 0.005 ppm.

Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 0.005 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 0.01 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 0.5 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 1 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 2 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 3 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 4 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 5 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 6 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 7 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 8 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 9 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 10 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 11 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 12 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 13 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 14 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 15 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 16 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 17 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 18 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve the sweetness of the comestible product is from 19 to 20 ppm.

In some embodiments, the amount effective to convey, enhance or improve the sweetness of the edible product is 0.001ppm, or 0.005ppm, or 0.01ppm, or 0.05ppm, or 0.1ppm, or 0.5ppm, or 1ppm, or 2ppm, or 3ppm, or 4ppm, or 5ppm, or 6ppm, or 7ppm, or 8ppm, or 9ppm, or 10ppm, or 11ppm, or 12ppm, or 13ppm, or 14ppm, or 15ppm, or 16ppm, or 17ppm, or 18ppm, or 19ppm, or 20 ppm.

In some forms, the amount effective to convey, enhance or improve the sweetness of the comestible product is 2 ppm.

In some forms, the present disclosure provides the use of a composition according to the aforementioned forms and embodiments thereof to communicate, enhance or improve perception of sweetness in a subject in need thereof.

In some forms, the present disclosure provides a method of communicating, enhancing or improving perception of sweet taste in a subject in need thereof, comprising the step of contacting the subject with a composition according to any one of the foregoing forms and embodiments thereof in an amount effective to communicate, enhance or improve the perception of sweet taste by the subject. In some embodiments, the subject is a human. In some embodiments, contacting comprises oral administration.

In some embodiments, the amount effective to convey, enhance or improve perception of sweetness in a subject is 0.001 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 0.001 to 19 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 0.001 to 18 ppm. Alternatively, an effective amount effective to convey, enhance or improve sweetness perception in a subject is 0.001 to 17 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 0.001 to 16 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 0.001 to 15 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 0.001 to 14 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 0.001 to 13 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 0.001 to 12 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 0.001 to 11 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 0.001 to 10 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 0.001 to 9 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 0.001 to 8 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 0.001 to 7 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 0.001 to 6 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 0.001 to 5 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 0.001 to 4 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 0.001 to 3 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 0.001 to 2 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 0.001 to 1 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 0.001 to 0.5 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 0.001 to 0.01 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 0.001 to 0.005 ppm.

Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 0.005 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 0.01 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 0.5 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 1 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 2 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 3 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 4 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 5 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 6 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 7 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 8 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 9 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 10 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 11 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 12 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 13 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 14 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 15 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 16 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 17 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 18 to 20 ppm. Alternatively, the amount effective to convey, enhance or improve perception of sweetness in the subject is 19 to 20 ppm.

In some forms, the amount effective to convey, enhance or improve perception of sweetness in a subject is 0.001ppm, or 0.005ppm, or 0.01ppm, or 0.05ppm, or 0.1ppm, or 0.5ppm, or 1ppm, or 2ppm, or 3ppm, or 4ppm, or 5ppm, or 6ppm, or 7ppm, or 8ppm, or 9ppm, or 10ppm, or 11ppm, or 12ppm, or 13ppm, or 14ppm, or 15ppm, or 16ppm, or 17ppm, or 18ppm, or 19ppm, or 20 ppm.

In some forms, the amount effective to convey, enhance or improve perception of sweetness in a subject is 2 ppm.

The present invention is best illustrated but is not limited to the following illustrative examples.

Examples

Example 1: purification of a composition comprising polymethoxylated flavones according to some of the modalities presented herein

Purification of HMQ and TMS: the distillate residue of 60 grams of orange oil was dissolved in 200mL cyclohexane. An equal volume of methanol was added and liquid-liquid extraction was performed. The methanol fraction was collected and designated "extract 1".

Extract 1 was dissolved in 15mL ethyl acetate and loaded onto a silica gel column. A gradient elution was then performed, starting with cyclohexane and ending with a 1:1 ratio of cyclohexane to ethyl acetate. The last two sub-fractions "F4" and "F5" were collected and loaded onto preparative HPLC with reverse phase column using solution system a-water and B-acetonitrile, 3,5,6,7,3',4' -Hexamethoxyflavone (HMQ) and 5,6,7,4 '-Tetramethoxyflavone (TMS) were purified from sub-fraction F4 on phenomenex preparative C18(2) (150 x 21.20mm 5 μm) column, while 5,6,7,4' -Tetramethoxyflavone (TMS) was purified from sub-fraction F5 on phenomenex preparative FPF (2) column (150 x 21.20mm x 5 μm). The identity of the purified polymethoxyflavone (5,6,7,4' -Tetramethoxyflavone (TMS) and 3,5,6,7,3',4' -Hexamethoxyflavone (HMQ)) has been confirmed by NMR and MS spectroscopy.

Purification of HMQ and TMS mixture: 10g of the orange oil distillate was extracted with 990g of 50% (w/w) aqueous ethanol. The extracted solution was filtered and concentrated under reduced pressure. The dried extract contains 5,6,7,4' -Tetramethoxyflavone (TMS) and 3,5,6,7,3',4' -Hexamethoxyflavone (HMQ) as well as other polymethoxylated flavones.

Example 2: purification and organoleptic properties of compositions comprising polymethoxylated flavones according to some of the modalities presented herein

Purification of polymethoxylated flavones including HMQ, TMS, and mixtures of HMQ and TMS: 100g of a distillate residue of orange oil was added to 1900g of a 50% (w/w) ethanol aqueous solution, and solid-liquid extraction was performed. The extracted solution was filtered and dried under reduced pressure. The dried extract comprises a mixture of polymethoxylated flavones.

20 grams of the dried extract was dissolved in 50mL of ethanol and the solution was applied to a silica gel column. The solvent system contained a cyclohexane (2000mL) and B cyclohexane/ethanol solutions in a ratio of 4:1 (1500 mL). A gradient elution was performed using a starting elution solution containing solvent a and ending with solvent B. A total of 16 sub-fractions were obtained and subjected to UPLC-UV analysis. The subfractions F9, F14 and F15 were collected and applied to various reverse phase preparative HPLC columns to isolate and purify various polymethoxylated flavones.

Solvent systems a-water and B-acetonitrile were used for peak separation by preparative HPLC with phenomenex C18(2) columns (150 x 21.20mm x 5 μm) or FPF (2) columns (150 x 21.20mm x 5 μm). 42.1mg of 3,5,6,7,3',4' -hexamethoxyflavone (hexamethoxyquercetn, HMQ), 100mg of 5,6,7,4' -tetramethoxyflavone (tetra-O-methylscutellarein, TMS) and 152mg of 5,6,7,8,3',4' -hexamethoxyflavone (NOB) were isolated from the subfraction F14 using a phenomenex preparative C18(2) column; a gradient elution procedure (50% B to 85% B) was used for each separation. The peak was collected at UV 335nm using a fraction collector. 40mg of 5,6,7,3',4' -pentamethoxyflavone (sinensetin) was isolated from subfraction F15 using a phenomenex FPF (2) column (150 × 21.20mm × 5 μm); 220mg of 3,5,6,7,8,3',4' -Heptamethoxyflavone (HMF) and 120mg of 5,6,7,8,4' -pentamethoxyflavone (TAN) were separated from subfraction F9 using an FPF (2) column. Gradient elution procedure (55% B to 75% B) was used for each separation. The peak was collected at UV 335nm using a fraction collector. The structure of the isolated polymethoxylated flavones was determined by NMR and MS spectroscopy as shown below.

Sensory evaluation: the sensory panel consisted of 25 trained panelists. Panelists were asked to evaluate the sweet taste improving effect of isolated individual polymethoxylated flavones in a reference aqueous solution containing 4% sucrose. The taste characteristics (sweetness) of samples containing TMS, HMQ, NOB, HMF, TAN and SIN (all 5ppm) and mixtures containing polymethoxylated flavone mixtures (PMF mixture 10ppm) were evaluated by panelists on a scale of-5 to 5 (-5 for strong masking effect, 5 for strong enhancement effect, 0 for intensity of a reference aqueous solution containing 4% sucrose, referred to herein as sucrose base). The results are shown in table 1 below.

TABLE 1

Remarking: + 90% significant enhancement

+ 95% significant enhancement

A + 99% significant enhancement

No significant enhancement of NS

-90% significant negative impact

Ten (10) ppm of PMF blend was found to significantly enhance the sweetness of the sucrose base with 95% confidence using a nose clip. However, only 5ppm TMS, 5ppm HMQ and 5ppm NOB were observed to significantly enhance the sweetness of the sucrose base. Neither HMF nor SIN had significant sweetness enhancement. TAN has a negative impact on sweetness.

The contents of the PMF mixture were found to contain all six polymethoxylated flavones (TMS, HMQ, NOB, HMF, TAN and SIN) as determined by reverse phase HPLC using a Luna C18(2) column and a UV detector (330nm UV). The HPLC chromatogram of the PMF mixture is shown in fig. 1.

Other sensory evaluations: the sensory panel consisted of 8 trained panelists. Panelists were asked to evaluate the sweet taste improving effect of 0.001, 0.1, 1, 2 and 20ppm of TMS, HMQ or NOB on a scale of-5 to 5 in a reference aqueous solution containing 4% sucrose (-5 for strong masking effect, 5 for strong enhancing effect, 0 for the strength of a reference aqueous solution containing 4% sucrose, referred to herein as sucrose base). The results are shown in table 2 below.

TABLE 2

Remarking: + 90% significant enhancement

+ 95% significant enhancement

A + 99% significant enhancement

No significant enhancement of NS

At a dosage of less than or equal to 2ppm, both TMS and HMQ have a better sweetness enhancing effect. Both TMS and HMQ had significant sweetness enhancing effect at 0.1 and 0.001 ppm. In contrast, the sweetness enhancing properties of NOB are less pronounced.

Other sensory evaluations: citrus oils typically contain more TMS than HMQ, while some may contain only TMS. The ratio of TMS to HMQ is typically between 2:1 and 6.5:1, with a maximum ratio of 25:1[ data from books of citrus oils [ edited by gionani Dugo and Luigi Mondello, chapter 8, the oxetane component of citrus essential oils ].

The sensory panel consisted of 8 trained panelists. Panelists were asked to evaluate the sweet taste improving effect of 0.5, 1, 2ppm TMS or HMQ and mixtures of different ratios of 1, 1.5, 2ppm TMS and HMQ in reference aqueous solutions containing 4% sucrose. The results are shown in table 3 below.

TABLE 3

Remarking: + 90% significant enhancement

+ 95% significant enhancement

A + 99% significant enhancement

No significant enhancement of NS

n.d. no available data

A 1:1 ratio of TMS to HMQ mixture was observed to have a better sweetness enhancing effect compared to 0.5ppm of TMS or HMQ. Similarly, a 1:1 ratio of TMS and HMQ mixture was observed to have a sweetness enhancing effect at a dose of 2ppm, however, unlike 1ppm of TMS alone, 1ppm of HMQ alone did not show any observable sweetness enhancing effect.

Other sensory evaluations: the sensory panel consisted of 8 trained panelists. Panelists were asked to evaluate the sweet taste improving effect of 0.001, 2 and 20ppm PMF blend, 0.2ppm TMS, 0.1ppm HMQ and 0.3ppm of a 2:1 ratio of TMS to HMQ blend in reference low-sugar fruit tea beverage solutions as well as in standard candy tea beverage solutions. The results are shown in table 4 below.

TABLE 4

Remarking: + 90% significant enhancement

+ 95% significant enhancement

A + 99% significant enhancement

No significant enhancement of NS

n.d. no available data

The difference between the sweetness intensity of standard sugar and the sweetness intensity of the tea beverage is obvious.

A mixture of TMS and HMQ at a 2:1 ratio was observed to have a sweetness enhancing effect at 0.3ppm, while HMQ alone at 0.1ppm showed no sweetness enhancing effect.

A sweetness enhancing effect was observed with the PMF blend at a dose of 2 ppm.

In conclusion, it was observed that a composition comprising a mixture of TMS and HMQ enhanced the sweetness of reduced sugar beverages over or similar to standard sugar beverages.

Publications cited throughout this document are hereby incorporated by reference in their entirety. While the various aspects of the present invention have been described above with reference to examples and preferred embodiments, it is to be understood that the scope of the invention is not to be limited by the foregoing description, but is to be defined by the appended claims appropriately interpreted under the doctrine of equivalents.

Other embodiments

G1.: a composition for sweetening or sweetness enhancing comprising tetra-O-methylscutellarein, hexamethoxyquercetn, or any mixture thereof, wherein the composition is a non-naturally occurring composition.

G2.: the composition of G1, wherein the composition comprises tetra-O-methyl scutellarein.

G3.: the composition of G1, wherein the composition comprises hexamethoxyquercet.

G4.: the composition of G1, wherein the composition comprises tetra-O-methyl scutellarein and hexamethoxyquercetn.

G5.: the composition of G4, wherein the composition comprises tetra-O-methyl scutellarein and hexamethoxyquercetn in a weight to weight ratio of 1:10 to 25:1, or 1:1 to 25:1, or 5:1 to 25: 1.

G6.: the composition of any one of G1 to G5, wherein the composition further comprises a liquid carrier, and wherein the composition is in liquid form.

G7.: the composition of G6, wherein the liquid carrier is water.

G8.: the composition of G6 or G7, wherein the composition is a solution or suspension.

G9.: the composition of any one of G6 to G8, wherein the composition optionally comprises undissolved solids.

G10: the composition of G9, wherein the composition comprises undissolved solids.

G11: the composition of G9 or G10, wherein the undissolved solid is in particulate form.

G12: the composition of any one of G9 to G11, wherein at least 90 wt.%, or at least 95 wt.%, or at least 97 wt.%, or at least 99 wt.% of the undissolved solids in the composition have a particle size of no more than 150 μ ι η, or no more than 106 μ ι η, or no more than 63 μ ι η, based on the total weight of the composition, wherein the particle size is measured as dry solids according to ISO 3310-1.

G13: the composition of any one of G6 to G8, wherein the composition is free of undissolved solids having a particle size of greater than 150 μ ι η, or greater than 106 μ ι η, or greater than 63 μ ι η, or greater than 38 μ ι η, wherein the particle size is measured as dry solids according to ISO 3310-1.

G14: the composition of any one of G6 to G13, further comprising one or more additives.

G15: the composition of G14, wherein the one or more additives are selected from the group consisting of: starches, such as corn starch and potato starch; cellulose or derivatives thereof, such as sodium carboxymethyl cellulose, ethyl cellulose and cellulose acetate; gum tragacanth; dextrins, such as maltodextrin and icodextrin (icodextrin); gelatin; oils such as peanut oil, cottonseed oil, safflower oil, sesame oil, olive oil, corn oil and soybean oil; glycols, such as propylene glycol; polyols, such as glycerol, sorbitol, mannitol and polyethylene glycol; esters such as ethyl oleate and ethyl laurate; agar; buffering agents such as magnesium hydroxide and aluminum hydroxide; alginic acid; isotonic saline; ethanol; phosphate buffer; any other edible substance used in liquid formulations; and any combination thereof.

G16: the composition of any one of G6 to G15, wherein the composition is a liquid concentrate for use as a sweetener, sweetness enhancer, or flavoring agent.

G17: the composition of any one of G1 to G5, wherein the composition is in solid form.

G18: the composition of G17, wherein the composition further comprises a solid carrier.

G19: the composition of G15, wherein the solid carrier comprises starch, such as corn starch and potato starch; cellulose or derivatives thereof, such as sodium carboxymethyl cellulose, ethyl cellulose and cellulose acetate; gum tragacanth; dextrins, such as maltodextrin and icodextrin; gelatin; or any combination thereof.

G20: the composition of any one of G17 to G19, wherein the solid is an amorphous solid.

G21: the composition of any one of G17 to G19, wherein the solid is a crystalline solid.

G22: the composition of any one of G17 to G19, wherein the composition is a powdered concentrate for use as a sweetener, sweetness enhancer, or flavoring agent.

G23: the composition of any one of G1 to G22, further comprising one or more additional sweeteners.

G24: the composition of G23, wherein the one or more additional sweeteners comprise a caloric sweetener, such as sucrose, fructose, or a combination thereof.

G25: the composition of G23, wherein the one or more additional sweeteners comprise a non-caloric sweetener.

G26: the composition of G25, wherein the non-caloric sweetener is selected from the group consisting of: steviol glycosides, e.g., rebaudioside a, rebaudioside D and rebaudioside M; mogrosides, such as mogroside IV; sugar alcohols, such as erythritol, sucralose; saccharin; cyclamate; aspartame; neotame; edward sweet; acesulfame potassium; glycyrrhizin; inulin; maltodextrin; monatin; monellin; ostrin Gum of Eupatorium; pantoprazole; psicose; and any combination thereof.

G27: the composition of any one of G1 to G26, further comprising one or more additional sweetness enhancers, such as natural or synthetic sweetness enhancers.

G28: the composition of any one of G1 to G27, further comprising one or more bitterness masking agents, such as natural or synthetic bitterness masking agents.

G29: the composition of any one of G1 to G28, further comprising one or more cooling agents, such as natural (e.g., menthol) or synthetic cooling agents.

G30: the composition of any one of G1 to G30, wherein the sweetness of the 4% w/v sucrose base is enhanced when the composition is added to the 4% w/v sucrose base at a concentration of 0.001 to 20 ppm.

G31: a tabletop sweetener composition comprising the composition of any one of G1 to G30.

G32: the tabletop sweetener composition of G31, having no more than 50%, or no more than 40%, or no more than 30%, or no more than 20%, or no more than 10%, or no more than 5% of a caloric sweet component equivalent to the amount of sucrose.

G33: a packaged food or beverage product comprising the composition of any one of G1 to G30.

G34: the packaged food or beverage product of G33, wherein the composition of any one of G1 to G30 is present in an amount effective to deliver, enhance or improve the sweetness of the packaged food or beverage product.

G35: the packaged food or beverage product of G34, wherein the concentration of tetra-O-methyl scutellarein, hexamethoxyquercetn, or a combination thereof ranges from 0.001ppm to 20ppm based on the total weight of the packaged food or beverage product.

G36: the packaged food or beverage product of G34, wherein the concentration of tetra-O-methyl scutellarein, hexamethoxyquercet, or a combination thereof in the packaged food or beverage product is no more than 20ppm, or no more than 15ppm, or no more than 10ppm, or no more than 5ppm, based on the total weight of the packaged food or beverage product.

G37: use of the composition of any one of G1 to G30 to communicate, enhance or improve the sweetness of an edible product by introducing the composition into the edible product.

G38: use of G37, wherein the composition is introduced to the edible product in an amount such that the concentration of tetra-O-methylscutellarein, hexamethoxyquercetn, or a combination thereof ranges from 0.001ppm to 20ppm, based on the total weight of the edible product.

G39: use of G37, wherein the composition is introduced to the edible product in an amount such that tetra-O-methylscutellarein, hexamethoxyquercetn, or a combination thereof is present in the edible product at a concentration of no more than 20ppm, or no more than 15ppm, or no more than 10ppm, or no more than 5ppm, based on the total weight of the edible product.

G40: a method of communicating, enhancing or improving the sweetness of an edible product comprising introducing into the edible product a composition of any one of G1 to G30.

G41: the method of G40, comprising introducing the composition in an amount such that the concentration of tetra-O-methyl scutellarein, hexa-methoxy quercitrin, or a combination thereof ranges from 0.001ppm to 20ppm, based on the total weight of the edible product.

G42: use of G40 comprising introducing an amount of a composition such that tetra-O-methyl scutellarein, hexamethoxyquercitrin, or a combination thereof is present in the edible product at a concentration of no more than 20ppm, or no more than 15ppm, or no more than 10ppm, or no more than 5ppm, based on the total weight of the edible product.

Claims

1. Use of a composition for conveying, enhancing or improving the sweetness of an edible product by introducing the composition into the edible product, wherein the composition comprises tetra-O-methylscutellarein, hexamethoxyquercetn or any mixture thereof, wherein the composition is a non-naturally occurring composition.

2. The use of claim 1, wherein the composition comprises tetra-O-methyl scutellarein and hexamethoxyquercetn.

3. The use of claim 2, wherein the composition comprises tetra-O-methyl scutellarein and hexamethoxyquercetn in a weight to weight ratio of 1:10 to 25: 1.

4. Use according to any one of claims 1 to 3, wherein the composition further comprises a liquid carrier, and wherein the composition is in liquid form.

5. The use of claim 4, wherein the composition optionally comprises an insoluble solid.

6. Use according to claim 5, wherein the composition is free of undissolved solids having a particle size of more than 150 μm, wherein the particle size is measured as dry solids according to ISO 3310-1.

7. Use according to any one of claims 4 to 6, wherein the composition is a liquid concentrate for use as a sweetener, sweetness enhancer or flavouring agent.

8. Use according to any one of claims 1 to 3, wherein the composition is in solid form.

9. The use of claim 8, wherein the composition further comprises a solid carrier.

10. Use according to claim 8 or 9, wherein the composition is a powdered concentrate for use as a sweetener, sweetness enhancer or flavoring agent.

11. Use according to any one of claims 1 to 10, wherein the composition further comprises one or more additional sweeteners.